NP-MRD: Showing NP-Card for withawrightolide (NP0043284)

Jump To Section:

Identification Spectra BioTaxonomy ChemoTaxonomy Physical properties Links References XML

Record Information

Version

2.0

Created at

2021-06-21 00:44:10 UTC

Updated at

2021-06-30 00:18:53 UTC

NP-MRD ID

NP0043284

Secondary Accession Numbers

None

Natural Product Identification

Common Name

withawrightolide

Provided By

JEOL Database JEOL Logo

Description

(1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0²,⁷.0⁵,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]Nonan-3-one belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton. withawrightolide is found in Datura wrightii. withawrightolide was first documented in 2013 (Zhang, H., et al.). Based on a literature review very few articles have been published on (1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0²,⁷.0⁵,⁷.0¹¹,¹⁵]Heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]Nonan-3-one.

Structure

MOL 3D MOL SDF 3D SDF PDB SMILES InChI


  Mrv1652306212102443D          

 71 77  0  0  0  0            999 V2000
   -1.4639   -1.9571    6.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816   -0.8917    6.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2667    6.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.2888    7.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    1.3096    5.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345    1.4054    4.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0588    0.6856    4.4219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7823   -0.7775    4.7436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0700   -1.5767    4.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -1.2985    3.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.6532    3.8438 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3481    0.8525    3.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0378    1.2168    2.1079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859    2.7615    1.9301 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4155    3.1085    0.5254 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5497    1.7572   -0.1545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3864    1.6762   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8685    2.6542   -2.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6979    2.5853   -3.7774 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    3.0735   -3.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092    1.1867   -4.3208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431    1.0766   -5.7810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8623    0.6599   -5.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5856   -0.7988   -5.1502 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5384   -1.1992   -4.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.3635   -3.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0464   -3.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6338   -0.1108   -3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.2254   -1.9890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6869   -0.8059   -0.8940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9112   -0.6159    0.4225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0434    0.8164    0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5005    1.0828    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -1.9769    7.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.8532    6.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    2.4744    4.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    1.1025    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    0.8076    3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -2.6564    4.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714   -1.3001    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.4066    3.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067   -1.1404    3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -0.8540    4.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    1.3035    3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.7772    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    3.0703    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.3108    2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    3.6298    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    3.7664    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.4540   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    1.9361   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806    2.4305   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    3.6771   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.2583   -4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    3.0178   -4.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.9813   -6.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.3130   -6.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114    1.2403   -5.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.9535   -4.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -1.3827   -6.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1614   -4.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.0338   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    0.7306   -2.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.0363   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879   -1.8207   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -0.7638   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.3593    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.8552    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.0059    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    2.0787    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    0.3559    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 32  1  0  0  0  0
 19 18  1  0  0  0  0
 27 28  1  1  0  0  0
 18 17  1  0  0  0  0
 19 20  1  0  0  0  0
 29 17  1  0  0  0  0
 17 51  1  1  0  0  0
 21 22  1  6  0  0  0
 13 12  1  0  0  0  0
 27 25  1  0  0  0  0
 12  6  1  0  0  0  0
  6  5  1  0  0  0  0
 27 21  1  0  0  0  0
 29 30  1  0  0  0  0
 17 16  1  0  0  0  0
 32 31  1  0  0  0  0
  6  7  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2  8  1  0  0  0  0
  8  7  1  0  0  0  0
 31 30  1  0  0  0  0
 29 64  1  6  0  0  0
 32 16  1  0  0  0  0
 16 50  1  6  0  0  0
 24 23  1  0  0  0  0
 32 33  1  1  0  0  0
 24 25  1  0  0  0  0
 12 11  1  0  0  0  0
 23 22  1  0  0  0  0
  8  9  1  1  0  0  0
 27 29  1  0  0  0  0
  2  1  2  3  0  0  0
 21 19  1  0  0  0  0
  3  4  2  0  0  0  0
 16 15  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 15 14  1  0  0  0  0
 25 26  2  0  0  0  0
 23 21  1  0  0  0  0
 14 13  1  0  0  0  0
  6 36  1  6  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 23 58  1  6  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
 19 54  1  6  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
 30 65  1  0  0  0  0
 30 66  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 13 45  1  6  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 20 55  1  0  0  0  0
 12 44  1  1  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 33 71  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
   -1.4639   -1.9571    6.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816   -0.8917    6.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2667    6.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.2888    7.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    1.3096    5.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345    1.4054    4.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0588    0.6856    4.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.7775    4.7436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0700   -1.5767    4.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -1.2985    3.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.6532    3.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481    0.8525    3.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0378    1.2168    2.1079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859    2.7615    1.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155    3.1085    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    1.7572   -0.1545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3864    1.6762   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8685    2.6542   -2.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.5853   -3.7774 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    3.0735   -3.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092    1.1867   -4.3208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431    1.0766   -5.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.6599   -5.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5856   -0.7988   -5.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384   -1.1992   -4.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.3635   -3.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0464   -3.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6338   -0.1108   -3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.2254   -1.9890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6869   -0.8059   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -0.6159    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    0.8164    0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5005    1.0828    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -1.9769    7.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.8532    6.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    2.4744    4.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    1.1025    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    0.8076    3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -2.6564    4.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714   -1.3001    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.4066    3.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067   -1.1404    3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -0.8540    4.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    1.3035    3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.7772    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    3.0703    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.3108    2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    3.6298    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    3.7664    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.4540   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    1.9361   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806    2.4305   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    3.6771   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.2583   -4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    3.0178   -4.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.9813   -6.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.3130   -6.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114    1.2403   -5.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.9535   -4.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -1.3827   -6.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1614   -4.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.0338   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    0.7306   -2.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.0363   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879   -1.8207   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -0.7638   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.3593    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.8552    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.0059    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    2.0787    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    0.3559    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 32  1  0
 19 18  1  0
 27 28  1  1
 18 17  1  0
 19 20  1  0
 29 17  1  0
 17 51  1  1
 21 22  1  6
 13 12  1  0
 27 25  1  0
 12  6  1  0
  6  5  1  0
 27 21  1  0
 29 30  1  0
 17 16  1  0
 32 31  1  0
  6  7  1  0
  5  3  1  0
  3  2  1  0
  2  8  1  0
  8  7  1  0
 31 30  1  0
 29 64  1  6
 32 16  1  0
 16 50  1  6
 24 23  1  0
 32 33  1  1
 24 25  1  0
 12 11  1  0
 23 22  1  0
  8  9  1  1
 27 29  1  0
  2  1  2  3
 21 19  1  0
  3  4  2  0
 16 15  1  0
  8 10  1  0
 10 11  1  0
 15 14  1  0
 25 26  2  0
 23 21  1  0
 14 13  1  0
  6 36  1  6
 24 59  1  0
 24 60  1  0
 23 58  1  6
 22 56  1  0
 22 57  1  0
 19 54  1  6
 18 52  1  0
 18 53  1  0
 31 67  1  0
 31 68  1  0
 30 65  1  0
 30 66  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 13 45  1  6
 28 61  1  0
 28 62  1  0
 28 63  1  0
 20 55  1  0
 12 44  1  1
  7 37  1  0
  7 38  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
 11 42  1  0
 11 43  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
  1 34  1  0
  1 35  1  0
M  END


  Mrv1652306212102443D          

 71 77  0  0  0  0            999 V2000
   -1.4639   -1.9571    6.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816   -0.8917    6.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2667    6.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.2888    7.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    1.3096    5.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345    1.4054    4.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0588    0.6856    4.4219 C   0  0  1  0  0  0  0  0  0  0  0  0
   -1.7823   -0.7775    4.7436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0700   -1.5767    4.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -1.2985    3.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.6532    3.8438 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.3481    0.8525    3.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0378    1.2168    2.1079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859    2.7615    1.9301 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.4155    3.1085    0.5254 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.5497    1.7572   -0.1545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3864    1.6762   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8685    2.6542   -2.5044 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6979    2.5853   -3.7774 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    3.0735   -3.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092    1.1867   -4.3208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431    1.0766   -5.7810 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.8623    0.6599   -5.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5856   -0.7988   -5.1502 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.5384   -1.1992   -4.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.3635   -3.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0464   -3.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6338   -0.1108   -3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.2254   -1.9890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6869   -0.8059   -0.8940 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.9112   -0.6159    0.4225 C   0  0  2  0  0  0  0  0  0  0  0  0
    1.0434    0.8164    0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5005    1.0828    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -1.9769    7.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.8532    6.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    2.4744    4.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    1.1025    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    0.8076    3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -2.6564    4.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714   -1.3001    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.4066    3.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067   -1.1404    3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -0.8540    4.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    1.3035    3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.7772    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    3.0703    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.3108    2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    3.6298    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    3.7664    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.4540   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    1.9361   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806    2.4305   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    3.6771   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.2583   -4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    3.0178   -4.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.9813   -6.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.3130   -6.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114    1.2403   -5.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.9535   -4.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -1.3827   -6.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1614   -4.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.0338   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    0.7306   -2.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.0363   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879   -1.8207   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -0.7638   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.3593    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.8552    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.0059    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    2.0787    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    0.3559    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 32  1  0  0  0  0
 19 18  1  0  0  0  0
 27 28  1  1  0  0  0
 18 17  1  0  0  0  0
 19 20  1  0  0  0  0
 29 17  1  0  0  0  0
 17 51  1  1  0  0  0
 21 22  1  6  0  0  0
 13 12  1  0  0  0  0
 27 25  1  0  0  0  0
 12  6  1  0  0  0  0
  6  5  1  0  0  0  0
 27 21  1  0  0  0  0
 29 30  1  0  0  0  0
 17 16  1  0  0  0  0
 32 31  1  0  0  0  0
  6  7  1  0  0  0  0
  5  3  1  0  0  0  0
  3  2  1  0  0  0  0
  2  8  1  0  0  0  0
  8  7  1  0  0  0  0
 31 30  1  0  0  0  0
 29 64  1  6  0  0  0
 32 16  1  0  0  0  0
 16 50  1  6  0  0  0
 24 23  1  0  0  0  0
 32 33  1  1  0  0  0
 24 25  1  0  0  0  0
 12 11  1  0  0  0  0
 23 22  1  0  0  0  0
  8  9  1  1  0  0  0
 27 29  1  0  0  0  0
  2  1  2  3  0  0  0
 21 19  1  0  0  0  0
  3  4  2  0  0  0  0
 16 15  1  0  0  0  0
  8 10  1  0  0  0  0
 10 11  1  0  0  0  0
 15 14  1  0  0  0  0
 25 26  2  0  0  0  0
 23 21  1  0  0  0  0
 14 13  1  0  0  0  0
  6 36  1  6  0  0  0
 24 59  1  0  0  0  0
 24 60  1  0  0  0  0
 23 58  1  6  0  0  0
 22 56  1  0  0  0  0
 22 57  1  0  0  0  0
 19 54  1  6  0  0  0
 18 52  1  0  0  0  0
 18 53  1  0  0  0  0
 31 67  1  0  0  0  0
 31 68  1  0  0  0  0
 30 65  1  0  0  0  0
 30 66  1  0  0  0  0
 15 48  1  0  0  0  0
 15 49  1  0  0  0  0
 14 46  1  0  0  0  0
 14 47  1  0  0  0  0
 13 45  1  6  0  0  0
 28 61  1  0  0  0  0
 28 62  1  0  0  0  0
 28 63  1  0  0  0  0
 20 55  1  0  0  0  0
 12 44  1  1  0  0  0
  7 37  1  0  0  0  0
  7 38  1  0  0  0  0
 33 69  1  0  0  0  0
 33 70  1  0  0  0  0
 33 71  1  0  0  0  0
 11 42  1  0  0  0  0
 11 43  1  0  0  0  0
  9 39  1  0  0  0  0
  9 40  1  0  0  0  0
  9 41  1  0  0  0  0
  1 34  1  0  0  0  0
  1 35  1  0  0  0  0
M  END
> <DATABASE_ID>
NP0043284

> <DATABASE_NAME>
NP-MRD

> <SMILES>
[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]4([H])C([H])([H])O[C@]5(C(=C([H])[H])C(=O)O[C@]4([H])C5([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@]2(C(=O)C([H])([H])[C@]3([H])C([H])([H])[C@]123)C([H])([H])[H]

> <INCHI_IDENTIFIER>
InChI=1S/C28H38O5/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23(30)28-11-15(28)9-22(29)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,30H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19-,20+,21-,23-,25+,26-,27+,28+/m1/s1

> <INCHI_KEY>
RWZUJIPMFKTTKN-BLMPNAGISA-N

> <FORMULA>
C28H38O5

> <MOLECULAR_WEIGHT>
454.607

> <EXACT_MASS>
454.271924324

> <JCHEM_ACCEPTOR_COUNT>
4

> <JCHEM_ATOM_COUNT>
71

> <JCHEM_AVERAGE_POLARIZABILITY>
50.80713276403658

> <JCHEM_BIOAVAILABILITY>
1

> <JCHEM_DONOR_COUNT>
1

> <JCHEM_FORMAL_CHARGE>
0

> <JCHEM_GHOSE_FILTER>
0

> <JCHEM_IUPAC>
(1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <ALOGPS_LOGP>
2.58

> <JCHEM_LOGP>
3.417935321333334

> <ALOGPS_LOGS>
-5.73

> <JCHEM_MDDR_LIKE_RULE>
0

> <JCHEM_NUMBER_OF_RINGS>
7

> <JCHEM_PHYSIOLOGICAL_CHARGE>
0

> <JCHEM_PKA>
19.334746172606568

> <JCHEM_PKA_STRONGEST_ACIDIC>
14.650884908993138

> <JCHEM_PKA_STRONGEST_BASIC>
-2.951491958916195

> <JCHEM_POLAR_SURFACE_AREA>
72.83000000000001

> <JCHEM_REFRACTIVITY>
122.35009999999998

> <JCHEM_ROTATABLE_BOND_COUNT>
1

> <JCHEM_RULE_OF_FIVE>
1

> <ALOGPS_SOLUBILITY>
8.46e-04 g/l

> <JCHEM_TRADITIONAL_IUPAC>
(1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one

> <JCHEM_VEBER_RULE>
0

$$$$

     RDKit          3D

 71 77  0  0  0  0  0  0  0  0999 V2000
   -1.4639   -1.9571    6.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816   -0.8917    6.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2667    6.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.2888    7.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    1.3096    5.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345    1.4054    4.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0588    0.6856    4.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.7775    4.7436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0700   -1.5767    4.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -1.2985    3.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.6532    3.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481    0.8525    3.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0378    1.2168    2.1079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859    2.7615    1.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155    3.1085    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    1.7572   -0.1545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3864    1.6762   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8685    2.6542   -2.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.5853   -3.7774 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    3.0735   -3.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092    1.1867   -4.3208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431    1.0766   -5.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.6599   -5.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5856   -0.7988   -5.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384   -1.1992   -4.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.3635   -3.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0464   -3.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6338   -0.1108   -3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.2254   -1.9890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6869   -0.8059   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -0.6159    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    0.8164    0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5005    1.0828    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -1.9769    7.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.8532    6.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    2.4744    4.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    1.1025    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    0.8076    3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -2.6564    4.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714   -1.3001    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.4066    3.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067   -1.1404    3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -0.8540    4.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    1.3035    3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.7772    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    3.0703    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.3108    2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    3.6298    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    3.7664    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.4540   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    1.9361   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806    2.4305   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    3.6771   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.2583   -4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    3.0178   -4.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.9813   -6.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.3130   -6.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114    1.2403   -5.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.9535   -4.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -1.3827   -6.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1614   -4.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.0338   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    0.7306   -2.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.0363   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879   -1.8207   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -0.7638   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.3593    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.8552    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.0059    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    2.0787    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    0.3559    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 32  1  0
 19 18  1  0
 27 28  1  1
 18 17  1  0
 19 20  1  0
 29 17  1  0
 17 51  1  1
 21 22  1  6
 13 12  1  0
 27 25  1  0
 12  6  1  0
  6  5  1  0
 27 21  1  0
 29 30  1  0
 17 16  1  0
 32 31  1  0
  6  7  1  0
  5  3  1  0
  3  2  1  0
  2  8  1  0
  8  7  1  0
 31 30  1  0
 29 64  1  6
 32 16  1  0
 16 50  1  6
 24 23  1  0
 32 33  1  1
 24 25  1  0
 12 11  1  0
 23 22  1  0
  8  9  1  1
 27 29  1  0
  2  1  2  3
 21 19  1  0
  3  4  2  0
 16 15  1  0
  8 10  1  0
 10 11  1  0
 15 14  1  0
 25 26  2  0
 23 21  1  0
 14 13  1  0
  6 36  1  6
 24 59  1  0
 24 60  1  0
 23 58  1  6
 22 56  1  0
 22 57  1  0
 19 54  1  6
 18 52  1  0
 18 53  1  0
 31 67  1  0
 31 68  1  0
 30 65  1  0
 30 66  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 13 45  1  6
 28 61  1  0
 28 62  1  0
 28 63  1  0
 20 55  1  0
 12 44  1  1
  7 37  1  0
  7 38  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
 11 42  1  0
 11 43  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
  1 34  1  0
  1 35  1  0
M  END

HEADER    PROTEIN                                 21-JUN-21   NONE
TITLE     NULL                                                        
COMPND    NULL                                                        
SOURCE    NULL                                                        
KEYWDS    NULL                                                        
EXPDTA    NULL                                                        
AUTHOR    Marvin                                                      
REVDAT   1   21-JUN-21         0                                  
HETATM    1  C   UNK     0      -1.464  -1.957   6.972  0.00  0.00           C+0
HETATM    2  C   UNK     0      -1.282  -0.892   6.168  0.00  0.00           C+0
HETATM    3  C   UNK     0      -0.546   0.267   6.754  0.00  0.00           C+0
HETATM    4  O   UNK     0      -0.183   0.289   7.924  0.00  0.00           O+0
HETATM    5  O   UNK     0      -0.275   1.310   5.930  0.00  0.00           O+0
HETATM    6  C   UNK     0      -0.735   1.405   4.559  0.00  0.00           C+0
HETATM    7  C   UNK     0      -2.059   0.686   4.422  0.00  0.00           C+0
HETATM    8  C   UNK     0      -1.782  -0.778   4.744  0.00  0.00           C+0
HETATM    9  C   UNK     0      -3.070  -1.577   4.482  0.00  0.00           C+0
HETATM   10  O   UNK     0      -0.808  -1.299   3.816  0.00  0.00           O+0
HETATM   11  C   UNK     0       0.466  -0.653   3.844  0.00  0.00           C+0
HETATM   12  C   UNK     0       0.348   0.853   3.595  0.00  0.00           C+0
HETATM   13  C   UNK     0       0.038   1.217   2.108  0.00  0.00           C+0
HETATM   14  C   UNK     0      -0.086   2.761   1.930  0.00  0.00           C+0
HETATM   15  C   UNK     0       0.416   3.108   0.525  0.00  0.00           C+0
HETATM   16  C   UNK     0       0.550   1.757  -0.155  0.00  0.00           C+0
HETATM   17  C   UNK     0       1.386   1.676  -1.439  0.00  0.00           C+0
HETATM   18  C   UNK     0       0.869   2.654  -2.504  0.00  0.00           C+0
HETATM   19  C   UNK     0       1.698   2.585  -3.777  0.00  0.00           C+0
HETATM   20  O   UNK     0       3.007   3.074  -3.505  0.00  0.00           O+0
HETATM   21  C   UNK     0       1.809   1.187  -4.321  0.00  0.00           C+0
HETATM   22  C   UNK     0       2.243   1.077  -5.781  0.00  0.00           C+0
HETATM   23  C   UNK     0       0.862   0.660  -5.369  0.00  0.00           C+0
HETATM   24  C   UNK     0       0.586  -0.799  -5.150  0.00  0.00           C+0
HETATM   25  C   UNK     0       1.538  -1.199  -4.035  0.00  0.00           C+0
HETATM   26  O   UNK     0       1.768  -2.364  -3.730  0.00  0.00           O+0
HETATM   27  C   UNK     0       2.124   0.046  -3.321  0.00  0.00           C+0
HETATM   28  C   UNK     0       3.634  -0.111  -3.129  0.00  0.00           C+0
HETATM   29  C   UNK     0       1.318   0.225  -1.989  0.00  0.00           C+0
HETATM   30  C   UNK     0       1.687  -0.806  -0.894  0.00  0.00           C+0
HETATM   31  C   UNK     0       0.911  -0.616   0.423  0.00  0.00           C+0
HETATM   32  C   UNK     0       1.043   0.816   0.977  0.00  0.00           C+0
HETATM   33  C   UNK     0       2.501   1.083   1.422  0.00  0.00           C+0
HETATM   34  H   UNK     0      -1.085  -1.977   7.991  0.00  0.00           H+0
HETATM   35  H   UNK     0      -1.976  -2.853   6.639  0.00  0.00           H+0
HETATM   36  H   UNK     0      -0.892   2.474   4.389  0.00  0.00           H+0
HETATM   37  H   UNK     0      -2.797   1.103   5.120  0.00  0.00           H+0
HETATM   38  H   UNK     0      -2.459   0.808   3.410  0.00  0.00           H+0
HETATM   39  H   UNK     0      -2.896  -2.656   4.555  0.00  0.00           H+0
HETATM   40  H   UNK     0      -3.871  -1.300   5.176  0.00  0.00           H+0
HETATM   41  H   UNK     0      -3.430  -1.407   3.460  0.00  0.00           H+0
HETATM   42  H   UNK     0       1.107  -1.140   3.113  0.00  0.00           H+0
HETATM   43  H   UNK     0       0.956  -0.854   4.803  0.00  0.00           H+0
HETATM   44  H   UNK     0       1.310   1.304   3.871  0.00  0.00           H+0
HETATM   45  H   UNK     0      -0.933   0.777   1.841  0.00  0.00           H+0
HETATM   46  H   UNK     0      -1.131   3.070   2.052  0.00  0.00           H+0
HETATM   47  H   UNK     0       0.508   3.311   2.669  0.00  0.00           H+0
HETATM   48  H   UNK     0       1.378   3.630   0.578  0.00  0.00           H+0
HETATM   49  H   UNK     0      -0.289   3.766   0.007  0.00  0.00           H+0
HETATM   50  H   UNK     0      -0.475   1.454  -0.428  0.00  0.00           H+0
HETATM   51  H   UNK     0       2.426   1.936  -1.212  0.00  0.00           H+0
HETATM   52  H   UNK     0      -0.181   2.430  -2.736  0.00  0.00           H+0
HETATM   53  H   UNK     0       0.910   3.677  -2.112  0.00  0.00           H+0
HETATM   54  H   UNK     0       1.252   3.258  -4.520  0.00  0.00           H+0
HETATM   55  H   UNK     0       3.512   3.018  -4.334  0.00  0.00           H+0
HETATM   56  H   UNK     0       2.333   1.981  -6.375  0.00  0.00           H+0
HETATM   57  H   UNK     0       2.957   0.313  -6.071  0.00  0.00           H+0
HETATM   58  H   UNK     0       0.011   1.240  -5.693  0.00  0.00           H+0
HETATM   59  H   UNK     0      -0.442  -0.954  -4.812  0.00  0.00           H+0
HETATM   60  H   UNK     0       0.791  -1.383  -6.051  0.00  0.00           H+0
HETATM   61  H   UNK     0       4.158  -0.161  -4.090  0.00  0.00           H+0
HETATM   62  H   UNK     0       3.885  -1.034  -2.596  0.00  0.00           H+0
HETATM   63  H   UNK     0       4.057   0.731  -2.572  0.00  0.00           H+0
HETATM   64  H   UNK     0       0.259   0.036  -2.228  0.00  0.00           H+0
HETATM   65  H   UNK     0       1.488  -1.821  -1.255  0.00  0.00           H+0
HETATM   66  H   UNK     0       2.759  -0.764  -0.676  0.00  0.00           H+0
HETATM   67  H   UNK     0       1.283  -1.359   1.131  0.00  0.00           H+0
HETATM   68  H   UNK     0      -0.146  -0.855   0.248  0.00  0.00           H+0
HETATM   69  H   UNK     0       3.216   1.006   0.599  0.00  0.00           H+0
HETATM   70  H   UNK     0       2.627   2.079   1.858  0.00  0.00           H+0
HETATM   71  H   UNK     0       2.814   0.356   2.179  0.00  0.00           H+0
CONECT    1    2   34   35                                                  
CONECT    2    3    8    1                                                  
CONECT    3    5    2    4                                                  
CONECT    4    3                                                            
CONECT    5    6    3                                                       
CONECT    6   12    5    7   36                                             
CONECT    7    6    8   37   38                                             
CONECT    8    2    7    9   10                                             
CONECT    9    8   39   40   41                                             
CONECT   10    8   11                                                       
CONECT   11   12   10   42   43                                             
CONECT   12   13    6   11   44                                             
CONECT   13   32   12   14   45                                             
CONECT   14   15   13   46   47                                             
CONECT   15   16   14   48   49                                             
CONECT   16   17   32   50   15                                             
CONECT   17   18   29   51   16                                             
CONECT   18   19   17   52   53                                             
CONECT   19   18   20   21   54                                             
CONECT   20   19   55                                                       
CONECT   21   22   27   19   23                                             
CONECT   22   21   23   56   57                                             
CONECT   23   24   22   21   58                                             
CONECT   24   23   25   59   60                                             
CONECT   25   27   24   26                                                  
CONECT   26   25                                                            
CONECT   27   28   25   21   29                                             
CONECT   28   27   61   62   63                                             
CONECT   29   17   30   64   27                                             
CONECT   30   29   31   65   66                                             
CONECT   31   32   30   67   68                                             
CONECT   32   13   31   16   33                                             
CONECT   33   32   69   70   71                                             
CONECT   34    1                                                            
CONECT   35    1                                                            
CONECT   36    6                                                            
CONECT   37    7                                                            
CONECT   38    7                                                            
CONECT   39    9                                                            
CONECT   40    9                                                            
CONECT   41    9                                                            
CONECT   42   11                                                            
CONECT   43   11                                                            
CONECT   44   12                                                            
CONECT   45   13                                                            
CONECT   46   14                                                            
CONECT   47   14                                                            
CONECT   48   15                                                            
CONECT   49   15                                                            
CONECT   50   16                                                            
CONECT   51   17                                                            
CONECT   52   18                                                            
CONECT   53   18                                                            
CONECT   54   19                                                            
CONECT   55   20                                                            
CONECT   56   22                                                            
CONECT   57   22                                                            
CONECT   58   23                                                            
CONECT   59   24                                                            
CONECT   60   24                                                            
CONECT   61   28                                                            
CONECT   62   28                                                            
CONECT   63   28                                                            
CONECT   64   29                                                            
CONECT   65   30                                                            
CONECT   66   30                                                            
CONECT   67   31                                                            
CONECT   68   31                                                            
CONECT   69   33                                                            
CONECT   70   33                                                            
CONECT   71   33                                                            
MASTER        0    0    0    0    0    0    0    0   71    0  154    0
END

RDKit          3D

71 77  0  0  0  0  0  0  0  0999 V2000
   -1.4639   -1.9571    6.9716 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.2816   -0.8917    6.1675 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.5462    0.2667    6.7539 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1826    0.2888    7.9244 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2746    1.3096    5.9296 O   0  0  0  0  0  0  0  0  0  0  0  0
   -0.7345    1.4054    4.5592 C   0  0  2  0  0  0  0  0  0  0  0  0
   -2.0588    0.6856    4.4219 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.7823   -0.7775    4.7436 C   0  0  2  0  0  0  0  0  0  0  0  0
   -3.0700   -1.5767    4.4821 C   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8078   -1.2985    3.8159 O   0  0  0  0  0  0  0  0  0  0  0  0
    0.4658   -0.6532    3.8438 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.3481    0.8525    3.5949 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.0378    1.2168    2.1079 C   0  0  1  0  0  0  0  0  0  0  0  0
   -0.0859    2.7615    1.9301 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.4155    3.1085    0.5254 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.5497    1.7572   -0.1545 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.3864    1.6762   -1.4392 C   0  0  2  0  0  0  0  0  0  0  0  0
    0.8685    2.6542   -2.5044 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.6979    2.5853   -3.7774 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.0068    3.0735   -3.5047 O   0  0  0  0  0  0  0  0  0  0  0  0
    1.8092    1.1867   -4.3208 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.2431    1.0766   -5.7810 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.8623    0.6599   -5.3687 C   0  0  1  0  0  0  0  0  0  0  0  0
    0.5856   -0.7988   -5.1502 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.5384   -1.1992   -4.0346 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.7681   -2.3635   -3.7302 O   0  0  0  0  0  0  0  0  0  0  0  0
    2.1238    0.0464   -3.3205 C   0  0  1  0  0  0  0  0  0  0  0  0
    3.6338   -0.1108   -3.1290 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.3184    0.2254   -1.9890 C   0  0  1  0  0  0  0  0  0  0  0  0
    1.6869   -0.8059   -0.8940 C   0  0  0  0  0  0  0  0  0  0  0  0
    0.9112   -0.6159    0.4225 C   0  0  0  0  0  0  0  0  0  0  0  0
    1.0434    0.8164    0.9769 C   0  0  2  0  0  0  0  0  0  0  0  0
    2.5005    1.0828    1.4215 C   0  0  0  0  0  0  0  0  0  0  0  0
   -1.0851   -1.9769    7.9914 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.9755   -2.8532    6.6388 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.8920    2.4744    4.3895 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.7971    1.1025    5.1195 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.4587    0.8076    3.4099 H   0  0  0  0  0  0  0  0  0  0  0  0
   -2.8960   -2.6564    4.5545 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.8714   -1.3001    5.1757 H   0  0  0  0  0  0  0  0  0  0  0  0
   -3.4296   -1.4066    3.4599 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.1067   -1.1404    3.1127 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9558   -0.8540    4.8034 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3097    1.3035    3.8710 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.9328    0.7772    1.8413 H   0  0  0  0  0  0  0  0  0  0  0  0
   -1.1305    3.0703    2.0518 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.5083    3.3108    2.6694 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.3779    3.6298    0.5779 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.2890    3.7664    0.0066 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4753    1.4540   -0.4281 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.4264    1.9361   -1.2122 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1806    2.4305   -2.7357 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.9099    3.6771   -2.1122 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2517    3.2583   -4.5196 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.5117    3.0178   -4.3336 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.3327    1.9813   -6.3749 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.9574    0.3130   -6.0709 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.0114    1.2403   -5.6932 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.4424   -0.9535   -4.8120 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.7908   -1.3827   -6.0509 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.1580   -0.1614   -4.0895 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.8846   -1.0338   -2.5962 H   0  0  0  0  0  0  0  0  0  0  0  0
    4.0573    0.7306   -2.5719 H   0  0  0  0  0  0  0  0  0  0  0  0
    0.2592    0.0363   -2.2280 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.4879   -1.8207   -1.2552 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.7587   -0.7638   -0.6757 H   0  0  0  0  0  0  0  0  0  0  0  0
    1.2829   -1.3593    1.1306 H   0  0  0  0  0  0  0  0  0  0  0  0
   -0.1456   -0.8552    0.2475 H   0  0  0  0  0  0  0  0  0  0  0  0
    3.2161    1.0059    0.5989 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.6269    2.0787    1.8580 H   0  0  0  0  0  0  0  0  0  0  0  0
    2.8141    0.3559    2.1785 H   0  0  0  0  0  0  0  0  0  0  0  0
 13 32  1  0
 19 18  1  0
 27 28  1  1
 18 17  1  0
 19 20  1  0
 29 17  1  0
 17 51  1  1
 21 22  1  6
 13 12  1  0
 27 25  1  0
 12  6  1  0
  6  5  1  0
 27 21  1  0
 29 30  1  0
 17 16  1  0
 32 31  1  0
  6  7  1  0
  5  3  1  0
  3  2  1  0
  2  8  1  0
  8  7  1  0
 31 30  1  0
 29 64  1  6
 32 16  1  0
 16 50  1  6
 24 23  1  0
 32 33  1  1
 24 25  1  0
 12 11  1  0
 23 22  1  0
  8  9  1  1
 27 29  1  0
  2  1  2  3
 21 19  1  0
  3  4  2  0
 16 15  1  0
  8 10  1  0
 10 11  1  0
 15 14  1  0
 25 26  2  0
 23 21  1  0
 14 13  1  0
  6 36  1  6
 24 59  1  0
 24 60  1  0
 23 58  1  6
 22 56  1  0
 22 57  1  0
 19 54  1  6
 18 52  1  0
 18 53  1  0
 31 67  1  0
 31 68  1  0
 30 65  1  0
 30 66  1  0
 15 48  1  0
 15 49  1  0
 14 46  1  0
 14 47  1  0
 13 45  1  6
 28 61  1  0
 28 62  1  0
 28 63  1  0
 20 55  1  0
 12 44  1  1
  7 37  1  0
  7 38  1  0
 33 69  1  0
 33 70  1  0
 33 71  1  0
 11 42  1  0
 11 43  1  0
  9 39  1  0
  9 40  1  0
  9 41  1  0
  1 34  1  0
  1 35  1  0
M  END

View in JSmol

Synonyms

Not Available

Chemical Formula

C₂₈H₃₈O₅

Average Mass

454.6070 Da

Monoisotopic Mass

454.27192 Da

IUPAC Name

(1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one

Traditional Name

(1R,5R,8R)-8-[(1S,2R,5S,7R,8R,10S,11S,14R,15S)-8-hydroxy-2,15-dimethyl-3-oxopentacyclo[8.7.0.0^{2,7}.0^{5,7}.0^{11,15}]heptadecan-14-yl]-5-methyl-4-methylidene-2,6-dioxabicyclo[3.3.1]nonan-3-one

CAS Registry Number

Not Available

SMILES

[H]O[C@]1([H])C([H])([H])[C@@]2([H])[C@]3([H])C([H])([H])C([H])([H])[C@]([H])([C@]4([H])C([H])([H])O[C@]5(C(=C([H])[H])C(=O)O[C@]4([H])C5([H])[H])C([H])([H])[H])[C@@]3(C([H])([H])[H])C([H])([H])C([H])([H])[C@]2([H])[C@]2(C(=O)C([H])([H])[C@]3([H])C([H])([H])[C@]123)C([H])([H])[H]

InChI Identifier

InChI=1S/C28H38O5/c1-14-24(31)33-21-12-26(14,3)32-13-17(21)19-6-5-18-16-10-23(30)28-11-15(28)9-22(29)27(28,4)20(16)7-8-25(18,19)2/h15-21,23,30H,1,5-13H2,2-4H3/t15-,16+,17+,18+,19-,20+,21-,23-,25+,26-,27+,28+/m1/s1

InChI Key

RWZUJIPMFKTTKN-BLMPNAGISA-N

Experimental Spectra

Spectrum Type	Description	Depositor Email	Depositor Organization	Depositor	Deposition Date	View
1D NMR	¹³C NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 500 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 100 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 200 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 300 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 400 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 600 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 700 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 800 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 900 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹³C NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum
1D NMR	¹H NMR Spectrum (1D, 1000 MHz, CDCl₃, simulated)	Wishart Lab	Wishart Lab	David Wishart	2021-06-20	View Spectrum

Predicted Spectra

Not Available

Chemical Shift Submissions

Not Available

Species

Species of Origin

Species Name	Source	Reference
Datura wrightii	JEOL database	Zhang, H., et al, J. Nat. Prod. 76, 445 (2013)

Chemical Taxonomy

Description

Belongs to the class of organic compounds known as steroid lactones. These are sterol lipids containing a lactone moiety linked to the steroid skeleton.

Kingdom

Organic compounds

Super Class

Lipids and lipid-like molecules

Class

Steroids and steroid derivatives

Sub Class

Steroid lactones

Direct Parent

Steroid lactones

Alternative Parents

Substituents

Steroid lactone
Androstane-skeleton
Delta valerolactone
Delta_valerolactone
Oxane
Cyclic alcohol
Enoate ester
Alpha,beta-unsaturated carboxylic ester
Secondary alcohol
Carboxylic acid ester
Ketone
Lactone
Organoheterocyclic compound
Carboxylic acid derivative
Oxacycle
Dialkyl ether
Ether
Monocarboxylic acid or derivatives
Alcohol
Organic oxide
Carbonyl group
Organooxygen compound
Hydrocarbon derivative
Organic oxygen compound
Aliphatic heteropolycyclic compound

Molecular Framework

Aliphatic heteropolycyclic compounds

External Descriptors

Not Available

Physical Properties

State

Not Available

Experimental Properties

Property	Value	Reference
Melting Point	Not Available	Not Available
Boiling Point	Not Available	Not Available
Water Solubility	Not Available	Not Available
LogP	Not Available	Not Available

Predicted Properties

Property	Value	Source
logP	2.58	ALOGPS
logP	3.42	ChemAxon
logS	-5.7	ALOGPS
pKa (Strongest Acidic)	14.65	ChemAxon
pKa (Strongest Basic)	-3	ChemAxon
Physiological Charge	0	ChemAxon
Hydrogen Acceptor Count	4	ChemAxon
Hydrogen Donor Count	1	ChemAxon
Polar Surface Area	72.83 Å²	ChemAxon
Rotatable Bond Count	1	ChemAxon
Refractivity	122.35 m³·mol⁻¹	ChemAxon
Polarizability	50.81 Å³	ChemAxon
Number of Rings	7	ChemAxon
Bioavailability	Yes	ChemAxon
Rule of Five	Yes	ChemAxon
Ghose Filter	No	ChemAxon
Veber's Rule	No	ChemAxon
MDDR-like Rule	No	ChemAxon

External Links

HMDB ID

Not Available

DrugBank ID

Not Available

Phenol Explorer Compound ID

Not Available

FoodDB ID

Not Available

KNApSAcK ID

Not Available

Chemspider ID

Not Available

KEGG Compound ID

Not Available

BioCyc ID

Not Available

BiGG ID

Not Available

Wikipedia Link

Not Available

METLIN ID

Not Available

PubChem Compound

71659139

PDB ID

Not Available

ChEBI ID

Not Available

Good Scents ID

Not Available

References

General References

Zhang, H., et al. (2013). Zhang, H., et al, J. Nat. Prod. 76, 445 (2013). J. Nat. Prod..

Showing NP-Card for withawrightolide (NP0043284)

MOL for NP0043284 (withawrightolide)

3D MOL for NP0043284 (withawrightolide)

3D SDF for NP0043284 (withawrightolide)

3D-SDF for NP0043284 (withawrightolide)

PDB for NP0043284 (withawrightolide)

3D PDB for NP0043284 (withawrightolide)

SMILES for NP0043284 (withawrightolide)

INCHI for NP0043284 (withawrightolide)

Structure for NP0043284 (withawrightolide)

3D Structure for NP0043284 (withawrightolide)